KR870003104A - Method for preparing tetrahydro-2-heterocycloalkyl-pyrido [4,3-b] indole - Google Patents

Method for preparing tetrahydro-2-heterocycloalkyl-pyrido [4,3-b] indole Download PDF

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KR870003104A
KR870003104A KR1019860007739A KR860007739A KR870003104A KR 870003104 A KR870003104 A KR 870003104A KR 1019860007739 A KR1019860007739 A KR 1019860007739A KR 860007739 A KR860007739 A KR 860007739A KR 870003104 A KR870003104 A KR 870003104A
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pyrido
indole
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hydrogen
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아브델-매기드 아보우- 매기드
라유니 파텔 우사
페터 스타인 라인하트
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죠지 드모트
아메리칸홈 프러덕츠 코포레이션
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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia

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Abstract

The compounds of formulain which R<sup>1</sup> is hydrogen, halogen, hydroxy, or alkyl; R<sup>2</sup> is substituted or unsubstituted pyridinyl, pyrazinyl, quinolinyl or quinoxalinyl and said substituents are alkyl, alkoxy, alkoxycarbonyl, halogen, cyano or nitro; R<sup>5</sup> and R<sup>6</sup> are independently, hydrogen, alkyl, phenyl, halophenyl, methylphenyl, trifluoromethylphenyl, cyanophenyl or nitrophenyl, with the proviso that one of R<sup>5</sup> and R<sup>6 </sup>is other than hydrogen; and n is an integer from 1 to 7; and the pharmaceutically acceptable salts thereof, are antipsychotic and anxiolytic agents.

Description

테트라하이드로-2-헤테로사이클로알킬-피리도 [4,3-b]인돌의 제조방법Method for preparing tetrahydro-2-heterocycloalkyl-pyrido [4,3-b] indole

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (14)

하기 일반식(Ⅱ)의 감마 카볼린을 알킬화하여 그룹 -(CH2)m-R2(여기서 R2는 후술하는 바와 같다)를 도입시키고 경우에 따라, 형성된 염기를 이의 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 하기 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염을 제조하는 방법.Gamma carbolines of formula (II) are alkylated to introduce a group-(CH 2 ) m -R 2 , where R 2 is as described below, and optionally the base formed is a pharmaceutically acceptable salt thereof. To a compound of the general formula (I) or a pharmaceutically acceptable salt thereof. 상기식에서, R1은 수소, 할로겐, 하이드록시 또는 탄소수 1내지 6의 알킬이고 ' R2는Wherein R 1 is hydrogen, halogen, hydroxy or alkyl of 1 to 6 carbon atoms and R 2 is 이며, R3는 수소, 탄소수 1내지 6의 알킬, 탄소수 1내지 6의 알콕시 또는 -CO2R4이고 ; R4는 탄소수 1내지 6의 알킬, 할로겐, 시아노 또는 니트로이며, R5는 수소, 탄소수 1내지 6의 알킬, 페닐, 또는 할로겐, 메틸, 트리플루오로메틸, 시아노 또는 니트로 그룹에 의해 치환된 페닐이고, R6는 수소, 페닐, 또는 메틸, 에틸, 메톡시, 에톡시, 할로겐, 트리플루오로메틸, 시아노 또는 니트로그룹에 의해 치환된 페닐이며, 단, R5및 R6중 하나는 수소가 아니고, n은 내지 7의 정수중 하나이다.R 3 is hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or —CO 2 R 4 ; R 4 is alkyl, halogen, cyano or nitro having 1 to 6 carbon atoms, R 5 is hydrogen, alkyl, phenyl having 1 to 6 carbon atoms, or substituted by halogen, methyl, trifluoromethyl, cyano or nitro group Phenyl, and R 6 is hydrogen, phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, halogen, trifluoromethyl, cyano or nitro group, provided that one of R 5 and R 6 Is not hydrogen and n is one of the integers from -7. 제1항에 있어서, 감마-카볼린을 일반식 X-(CH2)n-R2(여기서, R2는 제1항에서 정의한 바와같고 X는 보름 또는 염소이다)의 할로알킬 화합물 또는 일반식 CH2=CH-R2(여기서, R2는 제1항에서 정의한 바와 같다)의 비닐 화합물로 알킬화시키는 방법.The haloalkyl compound or general formula of claim 1, wherein gamma-carboline is a general formula X- (CH 2 ) n -R 2 , wherein R 2 is as defined in claim 1 and X is full or chlorine. A process for alkylating with a vinyl compound of CH 2 = CH-R 2 , wherein R 2 is as defined in claim 1. 제1항에 있어서, R1이 수소 또는 할로겐인 방법.The method of claim 1, wherein R 1 is hydrogen or halogen. 제3항에 있어서, R2가The compound of claim 3, wherein R 2 is 이고, R3는 수소, 탄소수 1내지 4의 알킬, 탄소수 1내지 4의 알콕시 또는 -CO2R4이며 R4가 탄소수 1내지 4의 알킬, 할로겐, 시아노 또는 니트로인 방법.And R 3 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or —CO 2 R 4 and R 4 is alkyl of 1 to 4 carbon atoms, halogen, cyano or nitro. 제4항에 있어서, R5가 수소, 페닐 또는 할로페닐이고 R6는 수소, 페닐 또는 할로페닐이며 단, R5및 R6중 하나는 수소가 아닌 방법.The method of claim 4, wherein R 5 is hydrogen, phenyl or halophenyl and R 6 is hydrogen, phenyl or halophenyl, wherein one of R 5 and R 6 is not hydrogen. 제5항에 있어서, n이 정수 2,3 또는 4인 방법.6. The method of claim 5, wherein n is an integer 2, 3 or 4. 제1항에 있어서, 8-플루오로-5-(4-플루오로페닐)2,3,4,5-테트라하이드로-1H-피리도[34,3-b]인돌을 미챌(Michael) 부가반응 조건하에 2-비닐피리딘을 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-2-[2-(2-피리디닐)에틸]-1H-피리도[4,3-b] 인돌을 제조하는 방법.The Michael addition reaction of claim 1 wherein 8-fluoro-5- (4-fluorophenyl) 2,3,4,5-tetrahydro-1H-pyrido [34,3-b] indole is challenged. Alkylated with 2-vinylpyridine under conditions, optionally converting the product into a pharmaceutically acceptable salt, 8-fluoro-5- (4-fluorophenyl) -2,3 A process for preparing 4,5-tetrahydro-2- [2- (2-pyridinyl) ethyl] -1 H-pyrido [4,3-b] indole. 제1항에 있어서, 2,3,4,5-테트라하이드로-4-페닐-1H-피리도[4,3-b]인돌을 약 염기존재하에 비양자성 용매중에서 4-피리디닐부틸 브로마이드를 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 2,3,4,5-테트라하이드로-4-페닐-2-[4-(4-피리디닐)부틸]-1H-피리도[4,3-b] 인돌을 제조하는 방법.A pyridinylbutyl bromide according to claim 1, wherein 2,3,4,5-tetrahydro-4-phenyl-1H-pyrido [4,3-b] indole is used in an aprotic solvent in the presence of about a base. By alkylation and optionally converting the product into a pharmaceutically acceptable salt, 2,3,4,5-tetrahydro-4-phenyl-2- [4- (4-pyridinyl) Butyl] -1H-pyrido [4,3-b] indole. 제1항에 있어서, 2,3,4,5-테트라하이드로-4-페닐-1H-피리도[4,3-b]인돌을 약 염기존재하에 비양자성 용매중에서 3-피리디닐프로필 브로마이드를 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로하여,2,3,4,5-테트라하이드로-4-페닐-2-[3-(3-피리디닐)프로필]-1H-피리도[4,3-b] 인돌을 제조하는 방법.A pyridinylpropyl bromide according to claim 1, wherein 2,3,4,5-tetrahydro-4-phenyl-1H-pyrido [4,3-b] indole is used in an aprotic solvent in the presence of about a base. To alkylate and optionally convert the product into a pharmaceutically acceptable salt. 2,3,4,5-tetrahydro-4-phenyl-2- [3- (3-pyridinyl) Propyl] -1H-pyrido [4,3-b] indole. 제1항에 있어서, 2,3,4,5-테트라하이드로-4-페닐-1H-피리도[4,3-b]인돌을 부가반응조건하에서 2-비닐피리딘을 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여 2,3,4,5-테트라하이드로-4-페닐-2-[2-(2-피리디닐)에틸]-1H-피리도[4,3-b] 인돌을 제조하는 방법.The method of claim 1, wherein the 2,3,4,5-tetrahydro-4-phenyl-1H-pyrido [4,3-b] indole is alkylated with 2-vinylpyridine under addition reaction conditions, Thus, 2,3,4,5-tetrahydro-4-phenyl-2- [2- (2-pyridinyl) ethyl] -1H-pyrido, characterized in that the product is converted to a pharmaceutically acceptable salt. A process for preparing [4,3-b] indole. 제1항에 있어서, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-1H-피리도[4,3-b]인돌을 미챌 부가반응 조건하에 2-비닐퀴놀린을 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-2-[2-(2-퀴놀리닐)에틸]-1H-피리도[4,3-b] 인돌을 제조하는 방법.The method according to claim 1, wherein 8-fluoro-5- (4-fluorophenyl) -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole is subjected to the addition reaction conditions. 8-fluoro-5- (4-fluorophenyl) -2,3,4 characterized by alkylation with 2-vinylquinoline, optionally converting the product to a pharmaceutically acceptable salt A process for preparing, 5-tetrahydro-2- [2- (2-quinolinyl) ethyl] -1H-pyrido [4,3-b] indole. 제1항에 있어서, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-1H-피리도[4,3-b]인돌을 약 염기 존재하에 비양자성 용매중에서 4-피리디닐부틸 브로마이드를 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-2-[4-(2-피리디닐)-부틸]-1H-피리도[4,3-b] 인돌을 제조하는 방법.The method of claim 1, wherein 8-fluoro-5- (4-fluorophenyl) -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole is quantified in the presence of a weak base. Alkylated with 4-pyridinylbutyl bromide in a magnetic solvent, optionally converting the product to a pharmaceutically acceptable salt, wherein 8-fluoro-5- (4-fluorophenyl)- A process for preparing 2,3,4,5-tetrahydro-2- [4- (2-pyridinyl) -butyl] -1 H-pyrido [4,3-b] indole. 제1항에 있어서, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-1H-피리도[4,3-b]인돌을 미챌 부가반응 조건하에 4-비닐피리딘을 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-2-[2-(4-피리디닐)에틸]-1H-피리도[4,3-b] 인돌을 제조하는 방법.The method according to claim 1, wherein 8-fluoro-5- (4-fluorophenyl) -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole is subjected to the addition reaction conditions. Alkylated with 4-vinylpyridine and optionally converting the product into a pharmaceutically acceptable salt, 8-fluoro-5- (4-fluorophenyl) -2,3,4 A process for preparing, 5-tetrahydro-2- [2- (4-pyridinyl) ethyl] -1H-pyrido [4,3-b] indole. 제1항에 있어서, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-1H-피리도[4,3-b]인돌을 미챌 부가반응 조건하에 2-비닐피라진을 사용하여 알킬화시키고, 경우에 따라, 생성물을 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 8-플루오로-5-(4-플루오로페닐)-2,3,4,5-테트라하이드로-2-[2-(2-피라지닐)-에틸]-1H-피리도[4,3-b] 인돌을 제조하는 방법.The method according to claim 1, wherein 8-fluoro-5- (4-fluorophenyl) -2,3,4,5-tetrahydro-1H-pyrido [4,3-b] indole is subjected to the addition reaction conditions. 8-fluoro-5- (4-fluorophenyl) -2,3,4 characterized by alkylation with 2-vinylpyrazine and optionally converting the product to a pharmaceutically acceptable salt. A process for preparing, 5-tetrahydro-2- [2- (2-pyrazinyl) -ethyl] -1H-pyrido [4,3-b] indole. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019860007739A 1985-09-16 1986-09-15 Tetrahydro-2-heterocycloalkyl-pyrido(4,3-b)indol and preparation there of KR900002246B1 (en)

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US06/776,349 US4672117A (en) 1985-09-16 1985-09-16 Antipsychotic gamma-carbolines
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DE3674721D1 (en) 1990-11-08
GB2180535B (en) 1989-04-05
EP0222474B1 (en) 1990-10-03
DK440486A (en) 1987-03-17
GB2180535A (en) 1987-04-01
ATE57184T1 (en) 1990-10-15
ES2002617A6 (en) 1988-09-01
PT83345A (en) 1986-10-01
KR900002246B1 (en) 1990-04-07
US4672117A (en) 1987-06-09
ZA866259B (en) 1988-03-30
AU583941B2 (en) 1989-05-11
AU6181486A (en) 1987-03-19
HU194564B (en) 1988-02-29
PT83345B (en) 1988-07-29
EP0222474A1 (en) 1987-05-20
JPS6270374A (en) 1987-03-31
HUT42480A (en) 1987-07-28
GB8621225D0 (en) 1986-10-08
CA1275100A (en) 1990-10-09

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